Unlocking Your Dreams: Our Unfiltered Journey to Self-Employment and Entrepreneurial Success

Have you ever paused to envision a different path for your life? A life where Monday mornings spark excitement, not dread, and where your work feels less like an obligation and more like a passion you’ve meticulously built for yourself? A life so fulfilling that you don’t feel the constant need for an escape? For the past four years, this has been the very life my husband and I have actively pursued, and I’m thrilled to share that it’s not only attainable but also incredibly rewarding. It demands hard work, but the satisfaction is immeasurable.

Today, I’m stepping away from my usual recipes to delve into a topic deeply personal to me: our story as entrepreneurs. I’ve contemplated writing this post many times, eager to offer my honest advice and unique insights to anyone contemplating the leap into self-employment. My hope is to inspire more individuals to chase their dreams, no matter how daunting they may seem. While I may not be the most eloquent writer, I genuinely hope my passion for this subject shines through and provides a beacon of encouragement. For those unfamiliar with our journey, let’s start with a brief overview.

Our Entrepreneurial Journey to Full-Time Self-Employment

You can learn more about how Robbie and I met, and delve deeper into our personal story on my about me page. Our transition to a 100% self-employed family officially happened in March of 2017, a little over two years into our marriage. It was, without exaggeration, absolutely terrifying for me. When Robbie decided to resign from his part-time job, I was physically sick with worry. We had an eight-month-old son, a mortgage, existing debt, and the ever-present stack of general life expenses to consider.

Life, as we all know, is expensive.

Becoming self-employed is a significant leap, but navigating self-employment with a baby felt like the most frightening venture I had ever undertaken. The weight of knowing a small child depends entirely on you for everything, coupled with the desire to provide him with the best possible life, brought an immense amount of stress.

But the reward? It was undeniably worth every single moment of anxiety.

They say opposites attract, and this couldn’t be more true for Robbie and me. He is a decade my senior, a man who is consistently calm, composed, self-confident, optimistic, and laid-back. In contrast, I am essentially a walking bundle of anxiety, perpetually grappling with self-confidence, a pessimist by nature, and the complete antithesis of “chill.” Life certainly has a humorous way of pairing us!

Yet, all our differences create a perfect balance. I bring the business acumen, a love for numbers, and I help him expand his vision and grasp the broader scope of his business. I built his website, established his presence on Google, assist with scheduling, help quote jobs, manage all the finances, and ensure he stays organized. Where my nature leans towards pessimism, he is the unwavering source of encouragement and optimism. When I feel on the verge of giving up, he reassures me with steadfast confidence that I will succeed, and that he is incredibly proud of my efforts.

Even before we were married, just eight months into knowing each other and engaged, he actively encouraged me to pursue my aspirations. When I quit the job I detested the week before our wedding, he was my most enthusiastic cheerleader. This entire journey, from dream to reality, would simply not have been possible without each other’s unwavering support. Together, we are both living our dream careers and building a life that fills us with immense pride!

The Unconventional Leap into Entrepreneurship

If you had asked me in February of 2017 about our long-term goals, I would have confidently stated that we hoped to be fully self-employed within five years. The very next month, we made the monumental leap. As you can imagine, that was an extraordinarily intense and whirlwind period for us!

As someone who inherently craves stability and security, I often find myself comically reflecting on the unconventional nature of my current life. Robbie and I have never truly followed a conventional path, so perhaps it shouldn’t surprise me anymore that every year brings radical changes, and I don’t foresee that slowing down anytime soon. Here’s a brief summary of our rapidly evolving lives over the past few years, illustrating just how quickly things can transform:

• 2014: We had our first date, got engaged, and married. This was also the year I tentatively started my blog.
• 2015: Robbie transitioned to a new job, we purchased our first house, and excitedly discovered we were expecting our first child.
• 2016: Our son, Crosby, was born. Shortly after my maternity leave ended, I made the decision to leave my part-time job that I worked from home.
• 2017: Robbie resigned from his part-time position, marking our full transition to self-employment. Remarkably, both of our businesses doubled their previous year’s income. Robbie’s lawn care business, in particular, earned more than five times what it had generated in 2014.
• 2018: We took a significant step by filing both businesses as S Corporations, successfully navigated another slow landscaper’s winter primarily on my blog income, and I began earning a full-time income from my blog. I have a strong feeling this year will bring even more incredible milestones!

It’s truly astounding when I reflect on where we were just three years ago; the progress often feels surreal.

I know many people who endlessly search for the ultimate “get rich quick” scheme, but I must regrettably state that such a thing simply doesn’t exist. Many mistakenly believe that blogging is an effortless path to instant wealth. However, like any profession, it requires years of dedicated learning, hands-on experience, honing your craft, and consistent hard work to achieve success. My journey to where I am today is a testament to that.

I am a steadfast believer in the profound advantages of being self-employed. I continuously strive not to take for granted the incredible privilege that, most of the time, my job doesn’t feel like “work” at all.

I don’t dread working; in fact, I actively crave it. My passion for what I do is so strong that I often find it challenging to take a break.

My genuine love for my work is both a blessing and a challenge. My biggest ongoing struggle is finding the delicate balance between work, life, and motherhood. I constantly desire to do more and work more, but the reality is, time is a finite resource. This level of fulfillment didn’t manifest overnight; it took over three years of consistent effort. I believe this timeframe is a realistic expectation for anyone aspiring to build a career around their passions.

Key Advice for Aspiring Entrepreneurs and Side Hustlers

Don’t Quit Your Day Job (Yet!)

Many individuals are eager to leap into full-time self-employment at the first opportunity, but this often leads to significant financial struggles trying to make ends meet. My strongest recommendation is to start what you love as a side hustle, dedicating every available moment to building it. This approach, in my opinion, is the smartest and most financially sound way to transition your life. The absence of immediate pressure to pay all your bills from your new venture is an enormous advantage, especially if you have a family to support.

Robbie worked other jobs for the first eight years of building his business. Similarly, I maintained a part-time job from home for over a year while I was diligently growing my blog. This provided an essential safety net and allowed me to contribute to my family’s financial well-being, for which I am incredibly thankful. The key takeaway here is that neither of us made an immediate jump into full-time self-employment, even though it was always our ultimate objective.

Embrace Continuous Learning

Knowledge is unequivocally power. The more you learn, the better equipped you are to assess whether your envisioned entrepreneurial path truly aligns with your goals and skills. Even once you are fully self-employed, the learning never stops. If you’re venturing into a field you’ve never tackled before, you must commit to doing the groundwork: research, study, and absorb all the intricate details associated with your chosen profession.

For me, even three years into my blogging career, I am constantly seeking out new information and evolving best practices. As a result, I’ve amassed over three years’ worth of concentrated blogging knowledge, covering everything from the nuances of entrepreneurship to photography, WordPress technicalities, SEO strategies, social media engagement, and so much more. Never, ever stop learning and actively pursuing new knowledge. If you’ve been doing things the same way for an extended period, make a conscious effort to seek out any new information you can find. More often than not, I discover there’s always more I could be doing or improving. The pursuit of knowledge is paramount to sustained success.

I’m excited to share some of my favorite podcasts and books that have significantly impacted my journey so far. If you have any excellent recommendations, please do share them! I always appreciate finding new sources of inspiration.

Recommended Books and Podcasts for Entrepreneurs

Awesome with Alison Podcast – I’m starting with this one because it was the first podcast I listened to religiously, and the one that truly transformed me into a podcast enthusiast. Alison is refreshingly funny, authentically real, delightfully a little bit crazy, and absolutely overflowing with awesome insights. The core goal of her podcast is to make you feel more awesome than you did before you tuned in, and I can attest that this has been profoundly true for me!

Last July marked a critical turning point for my business. I felt stuck, unable to advance to the next level. I was grappling with depression, stress, and simultaneously caring for an eleven-month-old son. I wasn’t proud of my progress and began to question the future of my blog. Honestly, I wondered if I truly possessed what it took to elevate it. Then, something clicked in my mind. I decided to set clear year-end goals for my business, and the results were life-changing. Not only did I gain a renewed sense of purpose, but I also prioritized my work (a significant challenge with a baby) and felt a powerful surge of inspiration.

Many days I would wake up in a bad mood or remain in one after caring for a fussy baby all morning, just waiting for naptime to finally get some work done. Motherhood is incredibly draining and, on some days, feels all-consuming. My go-to routine when I lacked motivation to work was to turn on the Awesome with Alison podcast. Literally, by the end of an episode, I would feel uplifted and shifted into a completely different, positive mindset. Your mind is an extraordinarily important tool for success, and I am still actively working on reshaping my thoughts and subconscious behaviors. I genuinely cannot recommend Alison enough for her incredibly encouraging words, not just for entrepreneurs, but for anyone aspiring to become the best version of themselves. Oh, and her husband Eric also features on the podcast, and he’s fantastic too!

Jon Acuff Books – You know that feeling when you discover an author whose work you simply adore and instantly want to read everything they’ve ever written? That was precisely my experience with Jon Acuff. I was actively searching for business-oriented books, and when I stumbled upon his titles, I was immediately hooked. His unique blend of humor and engaging writing style resonated deeply with me. I devoured his books as quickly as I could carve out the time to read them.

Among his impactful works, I would have to say the most life-changing book for me was “Finish.” It’s packed with invaluable, golden advice. If you’re a “serial starter” who struggles to complete projects, or if you’re looking to learn more effective strategies for accomplishing your goals, this book is an absolute must-read. Here are some links to his books on Amazon if you’d like to explore them further. (Please note: if you purchase through my affiliate links, I will receive a small percentage at no additional cost to you.)

• Finish: Give Yourself the Gift of Done
• Start: Punch Fear in the Face, Escape Average & Do Work That Matters
• Do Over: Rescue Your Work, Your Career, and Your Life
• Quitter: Closing the Gap Between Your Day Job & Your Dream Job

Here’s a powerful quote from his book “Start” that perfectly encapsulates his philosophy: “You don’t need to go back in time to be awesome; you just have to start right now. Regretting that you didn’t start earlier is a great distraction from moving on your dream today, and the reality is that today is earlier than tomorrow.”

The Goal Digger Podcast / Jenna Kutcher – This podcast is a relatively new discovery for me, one I stumbled upon just a few months ago after seeing another blogger recommend it. Jenna Kutcher is an accomplished photographer and entrepreneur who built a multi-million-dollar online business before the age of 30. She is incredibly down-to-earth, authentic, and while some episodes cater specifically to photographers, the podcast as a whole is brimming with valuable and encouraging information for anyone pursuing their entrepreneurial dreams. I follow Jenna on Instagram, and she is truly a ray of sunshine and a powerful advocate for body positivity. She’s one of those rare individuals whose voice simply makes you feel good and genuinely inspires me on my own journey of doing what I love. You can follow her Goal Digger Podcast Instagram here and her personal Instagram here.

Jen Sincero – Another author whose work profoundly resonates with me. I’ve read two of her books and am currently re-reading them because they are simply that good. While her language can be quite bold, and some parts might seem a little unconventional to certain readers, the overarching concepts of self-love and strategies for overcoming self-doubt are absolutely phenomenal. I honestly couldn’t put them down! Here are my Amazon affiliate links to her inspiring books:

• You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life
• You Are a Badass at Making Money: Master the Mindset of Wealth

One of my favorite Jen Sincero quotes perfectly captures her empowering message: “If you’re serious about changing your life, you’ll find a way. If you’re not, you’ll find an excuse.”

The War of Art by Steven Pressfield – This is another truly fantastic read, offering a wealth of practical advice specifically tailored for creatives and anyone battling resistance in their work.

Here are a few incredibly insightful quotes from this book:

“Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do. Remember one rule of thumb: the more scared we are of a work or calling, the more sure we can be that we have to do it.”

“Our job in this life is not to shape ourselves into some ideal we imagine we ought to be, but to find out who we already are and become it.”

“The most important thing about art is to work. Nothing else matters except sitting down every day and trying.”

The Food Blogger Pro Podcast – This is another highly valuable podcast, not just for food bloggers, but for all types of bloggers. They feature interviews with a diverse range of interesting individuals, and I always look forward to listening to new episodes, finding actionable insights.

The Theory of Content Podcast – A more recent addition to my listening rotation, this podcast is entirely dedicated to SEO, hosted by Joshua Unseth and Amber Bracegirdle, co-founder of my ad network, Mediavine. Upping my SEO game is a major focus for me this year, and I’m thoroughly enjoying this podcast for its practical and in-depth advice.

If you have any other book or podcast recommendations that have helped you on your journey, please don’t hesitate to share them! I’m always on the lookout for new, high-quality content to absorb and learn from.

Self-Reflective Advice: What I’d Tell My Younger Entrepreneurial Self

You Don’t Have to Know Exactly What You Want to Do to Start

I genuinely believe this paralyzes many people from ever beginning to pursue their dreams. We often feel an overwhelming need for a perfectly clear end goal before we even take the first step. However, the reality of an entrepreneurial journey is that the goal frequently evolves along the way. When I first launched my blog, it had a different (and, frankly, quite embarrassing) name, and I envisioned myself as a food and lifestyle blogger.

It took me a couple of years to truly realize that my deep-seated passion and primary focus lay firmly in food blogging. That’s where my heart truly belonged. While I still occasionally publish a lifestyle post, my deepest connection is with crafting recipes. If I had waited two years to even begin this blog, fearing I wasn’t “ready” or “perfect,” I would undoubtedly not be where I am today. There are quite a few older posts on this blog that make me cringe to revisit (everyone has to start somewhere, especially with photography!), but the crucial lesson is: you simply cannot wait until you are an expert at everything before you begin. Just start.

I am a significantly better photographer and cook now than I was three and a half years ago. Just like any skill, my abilities have massively improved through consistent, dedicated practice and a willingness to learn from every attempt.

Surround Yourself with Like-Minded Individuals

When you decide to embark on a fundamentally different path for your life, you might encounter considerable resistance and pushback from people who know you. There’s an actual psychological theory around this phenomenon: when someone observes another person actively chasing their dreams, they often feel an unconscious need to ridicule or discourage them. Sometimes, the root cause of this reaction is that the person, deep down, recognizes they aren’t pursuing their own long-held aspirations. Other times, it’s simply their attempt to keep you confined to the identity they’ve always known you as, rather than the person you aspire to become.

I used to roll my eyes when I heard someone proclaim that the key to transforming your life lay entirely in your thoughts, but I now know with 100% certainty that it is profoundly true.

If your immediate social circle doesn’t fully support the new identity and life you envision for yourself, then actively surround yourself with as many inspiring books and podcasts as you can access. As much as I wish I could physically connect with like-minded entrepreneurs like Alison and Jenna, listening to their wisdom while I work is an incredibly close second. So much of the essential foundation for success is cultivated within your own mindset.

Minimize Social Media Consumption

Easier said than done, right? My profession inherently involves significant daily use of social media, making it a necessary tool for my work. That being said, the more time I spend idly scrolling through Facebook and Instagram, the more I start to feel a pervasive sense of unease about myself and my life. Social media is a perilous trap, easily leading you down the path of comparing your carefully curated highlights to the everyday realities of others. The single best recommendation I can offer you is to watch the Instagram stories of Colin Kartchner. He has completely revolutionized my perspective on social media and has firmly convinced me that my children will not be exposed to smartphones during their teenage years. Just go watch, and allow your eyes to be truly opened.

If your aim is to create a new life and a new self, your focus must remain squarely on that objective, not on being pulled back into the familiar patterns and comparisons. I actively strive not to be the person I have always been; I aspire to so much more for myself. I am already vastly different from the person most people in my life used to know. To genuinely change your life, you must fundamentally change your habits and your mindset.

Whenever I find myself feeling discouraged or falling into the comparison trap, my personal motto is: “Eyes on your own paper.” I am by far the happiest and most fulfilled in my life when my energy is directed towards self-improvement and cherishing my family, rather than comparing my life and success to strangers and online personas.

Don’t Let Perfectionism Hold You Back

Ah, perfectionism, my old nemesis. For entrepreneurs, perfectionism is nothing short of toxic. The way it most profoundly affected me was through my prolonged struggle with food photography for years. If I didn’t capture a “perfect enough” picture, I simply refused to post the recipe. If I could rewind time, I would metaphorically shake myself and emphatically tell myself to post it anyway. Nothing will ever be 100% perfect, and you only hinder your own progress and potential if you endlessly wait to post that recipe or publish that website. Just do it.

I absolutely love this quote from Jon Acuff, which perfectly captures this sentiment: “90 percent perfect and shared with the world always changes more lives than 100 percent perfect and stuck in your head.”

Final Takeaways: The Realities of Entrepreneurship

I want to take a moment to truly acknowledge how incredible it feels to work for yourself. Here are some of my most cherished perks of the self-designed life that Robbie and I have meticulously built:

Perks of Being Self-Employed

• Passion-Driven Work: We genuinely love our jobs; they don’t feel like a chore.
• Excitement for Work: We eagerly anticipate starting our workday, a stark contrast to previous roles.
• Flexible Schedules: I have help with Crosby about 15 hours a week at home, but otherwise, I can schedule my work during naptime, evenings, or weekends, allowing for great adaptability.
• Constant Presence with Family: I have the immense privilege of always being home with Crosby.
• Weather-Proof Work Days: If it’s raining or snowing, Robbie stays home to play with Crosby, which allows me to get more focused work done.
• Seasonal Breaks: Robbie is home approximately 90% of the time during the winter months, as landscaping work slows significantly, providing invaluable family time.
• Freedom to Travel: We can take extended vacations for weeks, for example, over Christmas, without needing to ask a boss for permission or worry about limited PTO.
• Passive Income Potential: I can take a day off work and still generate significant income that day, thanks to the power of passive income streams.

That being said, being self-employed is undeniably hard. Here are some of the ways our lives, while fulfilling, are also significantly more challenging.

Downsides to Being Self-Employed

• No “Off Hours”: For Robbie, this often means returning client calls and preparing quotes after he’s come home from a full day of work. Some nights, it’s 9 p.m., Crosby is finally asleep, and we’re still sitting down, strategizing his schedule, emailing clients, and meticulously tracking business finances. For my blog, it means I almost never truly take a day off. There’s an endless list of tasks that never quite get finished. I frequently work nights and weekends, and I sometimes struggle to be fully present with my family because my mind is preoccupied with all the remaining tasks. This is something I’ve actively struggled with and am consciously working to improve. Even though I adore my job, I absolutely do not want my son growing up thinking I prioritized work over him. He will always, always be more important.
• The High Cost of Life: When you’re self-employed, not only are you responsible for securing and paying for your own health insurance, but you also bear the full responsibility for your retirement planning, all business expenses, additional self-employment taxes, estimated tax payments, and the comprehensive list of expenditures that come with running your own enterprise. The financial safety nets provided by traditional employment are simply absent.
• The Tax Maze: This brings me directly to taxes. The sheer complexity of taxes and the accounting side of being self-employed is enough to make any sane person want to retreat. By far, this has been our biggest hurdle, and I even studied business and accounting in college! My best advice is to hire a competent accountant as soon as you reach a point where you’re earning a full-time living or are ready to elevate your business. We finally did this in March, and holy cow, it has dramatically reduced my workload. However, even with an accountant, there’s still a significant amount to keep up with on the financial side of running two businesses. It is certainly not for the faint of heart! We also transitioned to S Corporations this year and arranged for our accountants to manage payroll from our company accounts to us. Setting all of this up was a major headache, but I believe it will make our financial lives considerably smoother in the long run.
• Direct Income Responsibility: It can be incredibly daunting to depend solely on yourselves to generate income. If it rains for a week straight, Robbie loses potential earnings. If it’s a slow season for advertising, my blog income might take a hit. While this is also a perk, in that you have the potential to earn far more than in a salaried position, it comes with the substantial pressure to consistently generate enough income to provide for your family’s needs.

That was quite a lot to share, and if you’ve made it all the way to the end of this post, I sincerely thank you for reading along!

I genuinely believe that if more people pursued what they truly loved, the world would undoubtedly be a happier, more vibrant place. Perhaps your aspiration is to work for yourself full-time, or maybe you simply need to dedicate more time to the activities that bring you joy outside of your current job. Whatever your situation, I sincerely hope this post has inspired you to envision and strive for more in your own life. I firmly believe in the transformative power of every individual making a conscious effort to love themselves more and to become the absolute best possible version of themselves they can be.

“You are perfect. To think anything less is as pointless as a river thinking that it’s got too many curves or that it moves too slowly or that its rapids are too rapid. Says who? You’re on a journey with no defined beginning, middle or end. There are no wrong twists and turns. There is just being. And your job is to be as you as you can be. This is why you’re here. To shy away from who you truly are would leave the world you-less. You are the only you there is and ever will be. I repeat, you are the only you there is and ever will be. Do not deny the world its one and only chance to bask in your brilliance.” – Jen Sincero

MORE FOOD BLOGGING AND ENTREPRENEURSHIP RESOURCES

• 20 Things I Learned in My First Year of Food Blogging
• My 2-Year Blogging Journey Recap
• Celebrating 3 Years: Entrepreneurial Reflections
• 5 Years In: My Career as a Food Blogger